


Natural 20

by DelightfullyDifficult



Category: Once Upon a Time (TV)
Genre: CScocktober, Captain Swan - Freeform, Dungeons and Dragons, F/M
Language: English
Status: Completed
Published: 2018-11-03
Updated: 2018-11-07
Packaged: 2019-08-17 06:15:51
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 5,700
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16510898
Author URL: https://archiveofourown.org/users/DelightfullyDifficult/pseuds/DelightfullyDifficult
Summary: Who knew a game of Dungeons and Dragons would lead to some late night fun on the rooftop?  (CSCocktoberfest submission)





	1. Chapter 1

**Author's Note:**

> This has been beta-read by the dedicated @mishasbabyminion! Check her out!

     ****

           For the millionth time, Emma cursed the unreliability of the Boston transit system, commonly referred to as the T, as she checked her phone and saw that the bus she needed was running over 10 minutes behind.  With a sigh, she shot off a text to Mary Margaret to let her know she was on her way.

           Her phone rang less than a minute later.

           “What station are you at?” Mary Margaret asked without any preamble.

           “Andrew,” Emma growled out.

           Emma figured out she was on speaker phone when she heard David relaying her location to another in the background.

           “Killian is still on his way as well and will pass right by Andrew.  He’s going to pick you up,” Mary Margaret told her.

           Emma groaned.  “I’m fine, Mary Margaret.  The 10 should be here soon,” she insisted.

            “Are you really that keen to have your toes run over by personal shopping carts?” Her friend asked.

           She had a point.  The 10 passed through South Bay Center and there would be dozens of people finishing their weekend shopping.  The bus would be packed on its way to the South End.

           “Fine,” Emma mumbled, resigned, “tell him I’ll be in the Tedeschi’s parking lot.”

           “Excellent!” Mary Margaret squealed.  “See you both soon.”

           With a deep sigh, Emma put her phone back in her jacket pocket and grabbed the canvas bag at her feet that contained the couple bottles of wine that were her contribution to this evening’s get together.

           As she crossed the street to get to the Tedeschi’s, Emma realized that she had no idea what type of car Killian drove.  Thus, she was left awkwardly inspecting each car that entered the lot for the increasingly familiar face of Killian Jones.

           Killian had joined Emma and her friends biweekly Dungeons and Dragons group a few months ago.  He’d never played before, but had jumped head first into playing a Rogue their party had desperately needed.  A flirty, light fingered Rogue who charmed and pick-pocketed almost any NPC they came across.

           His flirting hadn’t been contained to just the game, either.  He’d flirted shamelessly with both her and Ruby, the latter of which gave as good as she got despite her recent engagement.

           “All in good fun.  Dorothy knows I’ll never stray,” her friend had said with a saucy wink.  “Though,” Ruby had continued as she stared appreciatively at Killian’s backside, “it might be worth it.”

           Killian was a sexy man.  His just broad enough shoulders, slim waist, and very fine ass were all emphasized by the tailored shirts and skinny jeans he favored.  He always had a bit of dark scruff on his handsome face, obviously carefully maintained.  His British accent was just the bow on top of an already attractive package.

           And Killian knew it.

           His confidence in his own attractiveness was why Emma had resisted all of his advances.  She spent too much time chasing overconfident men who thought they could flirt their way out of her dragging them in.

           David said she was judging Killian too harshly.  That the playboy persona she saw was mostly an act and that he was really just an awkward nerd.  Which made some sense, since David wasn’t the type to be friends with an obnoxious womanizer, much less invite him to join their D&D game.

           Sometimes, she saw hints that what David said was true; Killian had spent 20 minutes trying to convince Jefferson that their party’s trip down the coast would take half the amount of time the campaign guide said it would because the speed estimate for the type of ship they were traveling on was grossly inaccurate.  His ringtone was the noise the TARDIS made, for goodness sake.

           Overall, Emma wasn’t sure what to make of Killian Jones just yet.  Though she did appreciate his willingness to rescue her from the perils of the local transit system on short notice.

           Emma spotted Killian just as he pulled into the parking lot and she couldn’t help but admire the classic Chevelle he drove.  She was a beauty.

           Killian had his car in park and was around the front to open the passenger door before Emma had a chance to protest.  This wasn’t really the neighborhood to leave a car with the keys in it even for a moment.

           “Your chariot, m’lady,” Killian said with a grin.

           Emma tried to hide the grin Killian’s theatrics caused, but failed.

           “Thanks for the ride,” she said earnestly when Killian got back behind the wheel.

           “It is my pleasure, Swan.”

           Killian carefully maneuvered his car out of the lot and toward the South End neighborhood of Boston with skill.  Emma personally hated driving in Boston.  Her old but trustworthy VW Bug usually only moved when the skip she was tracking left the city.

            At a red light, Killian partially turned his head toward her and asked, “Are you looking forward to the new campaign?”

           Emma didn’t bother trying to hide her grin this time.  “Very!  I’m interested in what type of characters everyone ends up with.”  

           In an attempt to keep David from playing yet another upstanding Lawful Good character, the six of them had agreed to play characters they didn’t make themselves.  So they’d drawn names out of a hat and could only hope that their friends hadn’t made them something too horrible.  Emma knew that Ruby had made a conflicted Tiefling sorcerer for David that would challenge his D&D skills.

           The light turned green and Killian turned his full attention back to the road.

           “I admit, I am a bit… apprehensive.  After all, I am still a novice at this.”

           Intrigued, Emma gazed at Killian from the corner of her eye.  His scarred left hand held the wheel while the other scratched behind his ear.

           “I’m sure you’ll manage,” Emma reassured him.  He’d struggle at first, she was sure, but she had confidence that he’d find a way to make the half-elf monk she’d made for him into his own.

           For the rest of the trip, they reminisced about one of Killian’s first sessions with them.  He’d forgotten to check a chest for traps and the resulting acid spray had nearly killed half of the party, who had been in bad shape after a lengthy dungeon crawl.  

           Miraculously, Killian was able to find street parking near Jefferson’s brownstone.  Emma helped Killian carry the beer he’d brought up to the house, where they were greeted by David and Mary Margaret.

           “You made excellent time!” Mary Margaret said as she pulled Emma into a hug.  “Wasn’t that much less of a hassle than taking the bus?”

           “Quite,” Emma agreed.

           Mary Margaret’s smile at Emma’s admission could have lit up the city.  She’d been trying, desperately, to convince Emma to give Killian a chance.  Not in a romantic way, she’d insisted, but as a friend.

           David’s arms wrapped around both Emma and his wife to join the hug.  “Now that everyone has arrived, let’s get started!” He steered them toward the dining room.

           There was a sumptuous collection of snacks and drinks on the sideboard.  Emma’s wine joined the two bottles already there, four different flavors of hummus, and a variety of crackers and cheese.  There would be, Emma knew, a selection of craft beers in the cooler that sat off to the side.  No Mountain Dew and Doritos for this group of nerds.

           Their Dungeon Master, Jefferson, sat at the head of the table, with two more members of the group, Ruby and Will, to his left.  Folders with each person’s name in Jefferson’s neat handwriting were placed before the remaining seats.

           “No peeking,” Jefferson warned just as Emma’s hand hovered over her folder.  He hadn’t even looked up from whatever fresh torture he was devising.

           Emma made a face, which elicited a laugh from Ruby.

           David tapped her on the shoulder.  “Wine or beer tonight, Emma?”

           “A beer, please,” she requested as she took her seat.  “Something new.”

           A dark bottle with a label reading “Skull Splitter” and a picture of a Viking appeared in front of her;

           “Really?”

           Killian chuckled behind her.  “I figured it was appropriate.”

           As soon as the rest of the group was settled with snacks and drinks, Jefferson allowed them all to open the folders containing their new characters.

           Ruby immediately broke out laughing.

           Will groaned and dropped his head to the table.

           Emma blinked a few more times than necessary as she processed that, for the foreseeable future, she would be playing a halfling chaotic good bard, with an unsurprising entertainer background.

           She hated bards.

           The class’s   were next to useless, as were most of their level one spells.  The only thing they were generally good for were healing, once they learned healing word, and being a distraction.

           To make it even worse, her character’s name was Piper… and her instrument of choice was a fucking pan flute.

           “Who hates me?” She groaned out.

           Mary Margaret patted her softly on the shoulder in comfort.  “I think it’ll be good for you, as a player, to learn the ins and outs of being a spellcaster.  You always stick with martial type characters.”

           “Is this revenge for accidentally getting you killed last campaign?” Emma accused.

           Her friend smiled sweetly.  “Of course not, Emma,” she insisted, but there was a gleam in Mary Margaret’s eye that Emma knew meant danger.

           Will tossed his character sheet into the middle of the table.  “At least you aren’t some stick-in-the-arse paladin who can’t even take a shit without his God’s say so.”

           Emma took a sip of her beer to hide her smile.  Will preferred sneaky, devious types.  They’d had to ban him from always playing a rogue, but somehow he always managed to make whatever he was playing morally corrupt.  A paladin was the exact opposite of what he was used to.  There would be no wanton killing or thievery for Will this campaign.

           “Who suggested this rubbish plan again?” Will continued to complain.

           “I, for one, think it’ll be quite fun to play this…” Mary Margaret’s words trailed off as she finally took a look at her character sheet.  “This... half-orc rogue who is a hired killer.”

           Almost the entire table erupted into laughter.

           Like her husband, Mary Margaret liked morally upright characters.  Rogues tended to walk the fine line between good and evil.

           “Killian,” David called across the table, “You’ve been quiet.  What torment are you saddled with?”

           The aforementioned Brit rubbed his chin one more time before looking up.  “A monk, mate.  One that has been ejected from his monastery to learn more about the world first hand and not from dusty old books.”

           David nodded appreciatively. 

           “You two have something in common, than.”

           Confusion must have been plain on Emma’s face because David clarified his remark with, “This guy bought a two bedroom condo because he needed more room to store the obscene amount of books he has.”

           A small blush spread across Killian’s cheeks, something Emma had never seen before.

           “Wouldn’t it be cheaper to just get ebooks?” Ruby asked.

           Killian nodded.  “That may be, for the newer or popular publications.  But a lot of the books I own are a bit too… niche, to be released digitally.  Or too old for the publishers to bother.”

           Though she wasn’t much of a reader herself, Emma had always appreciated the knowledge that books held.  Even with so much information available on the Internet, it was always slightly more satisfying, in Emma’s mind, to hold a physical copy of something in your hand.

           Emma would have loved to continue to learn more about this intriguing aspect of Killian Jones, but was prevented from doing so when Jefferson brought all their attention back to the game at hand.

           “Now then, this campaign starts in Faerun, on the Sword Coast…”

           The night passed quickly as their characters met, were recruited to hunt down a group of cultists, only to be kidnapped by said cultists, and barely escaped with all members of the party alive.

           It was past midnight when Jefferson called an end to the game for that session.  Three of the four bottles of wine were empty, all the beer had been consumed, and David had a small blob of hummus in his hair.  No one was drunk, but everyone except for Mary Margaret was more than a little tipsy.  Her friend had opted to stay sober in order to be able to drive herself and David home.

           “Are you sure you don’t want a ride?” Mary Margaret asked her again, despite the fact that she and David lived north of Boston in Medford, while Emma lived south, in Dorchester.  Taking Emma home would take them nearly an hour out of their way.  Way too long for Emma to accept their offer.

           “I’ll take an UBER.  Or if the surge pricing is too much, I’ll crash here,” Emma assured her friend.  Jefferson had long ago established that any of them were welcome to stay in one of the guest bedrooms after a game- something Emma had done more than once after the city had eliminated its short -lived, late-night train services.

           Emma gave Mary Margaret one last hug and shooed her out the door.  David was already dozing in the car.  Ruby was picked up by Dorothy, her adoring fiancé, and Will headed off on his own.  Soon only she, Killian, and Jefferson remained.

           She wandered back into the dining room and found Killian staring contemplatively at his character sheet. She sat down and opened both her UBER and Lyft apps.

           “Do I dare ask what the surge is right now?” Killian queried from across the table.

           Emma looked down at her phone.  Both apps had estimated that a ride home ( ) would be nearly $60.

           “Nope.”

            Killian leaned back in his chair and stretched his arms above his head, which gave Emma a great view of his flat stomach and the trail of hair that led downward.

           “I guess I’ll take Jefferson up on his offer of hospitality for the night.  I’ve had one too many to risk getting behind the wheel.  Do you know where our host has disappeared to so I may discuss accommodations?”

           Emma couldn’t help giggling at Killian’s verbose way of speaking, which had somehow gotten worse as the night wore on.  It made her wonder if he toned down his obviously extensive vocabulary most of the time and was simply too tired to bother anymore.

           “He’s likely downstairs,” she told him.  As he started to walk toward the stairs, she hastily added, “I call the room on the top floor.”

           “As you wish,” he called backed.

           Emma’s heart did a flip in her chest.

           _Oh no_ , she chastised herself.  That is not allowed. 

           Just because he said Westley’s token line from _The Princess Bride_ , that did not mean she could start having fuzzy feelings for Killian Jones.

            Grabbing one of the remaining beers- another Skull Splitter -Emma made her way to the top floor of Jefferson’s home.  Instead of heading to the bedroom, she continued up to the private, rooftop patio.  She laid down on the long, all-season couch Jefferson had up here and listened to the sounds of the city as she sipped her beer.

           Boston’s T may not run late at night, but that didn’t mean the city turned in early.  It was early summer, the heat and humidity not yet as oppressive as it would be later in the year, so the streets were still full of people.  Bits of conversation floated up to Emma from groups walking by.  She could hear an ambulance in the distance, likely heading to one of the numerous University affiliated hospitals in the area.

           She had just started to doze when she heard the door to the patio open.

           Killian stood in the doorway.  “Do you mind if I join you?”

           Emma sat up and curled her legs under her to make room for Killian on the couch.  He sat and stretched his legs out in front of him.  This was the most relaxed Emma had ever seen him.

           “Are you enjoying your Dungeons and Dragons experience so far?”

           Killian chuckled.  “Is it normal for the DM to threaten to kill everyone on the first day of a new campaign?”

           With a smile, Emma told him, “Only if you’re doing it right.”

           He nodded and sipped his beer.

           They sat in companionable silence until Killian said, “Thank you for making an interesting character for me.  I was afraid I would end up…”

           “With a worthless bard?” she interjected.

           That elicited a loud laugh.  “Your so-called worthless bard saved the party by seducing the cultist guard.”

           “I rolled a natural twenty.  Even Mary Margaret’s barbarian would have succeeded with that roll,” she demurred.

           “But she didn’t,” he reminded her.

           Unable to argue against that point, Emma raised her beer in acquiescence.

           A cramp suddenly shot up Emma’s leg.  She quickly uncrossed them, accidentally kicking Killian in the process.

           His brow knitted in concern.  “Are you alright?”

           “Just a cramp,” she reassured him as she tried to find a good position to massage the uncomfortable muscle in her calf.

           Killian set his beer aside and lifted her legs onto his lap.  He pressed his fingers into the tight muscle of her right leg, slowly massaging it.  Emma groaned when the cramp subsided. 

           “Better?”

           When she nodded, Killian eased up on the pressure, but continued to softly rub along the muscle.

           Emma brought her eyes up to meet his.  His pupils were wide in the low light, with only a hint of their normal blue visible.  His face was relaxed, but Emma could see a hint of apprehension.  His hand slid higher up her leg and he watched her face for any indication that this was not welcome.

           There were two paths ahead of her that Emma could see.  She could put a stop to Killian’s ministrations, say an awkward goodnight, and spend a sleepless night wondering if she’d made the right decisions.  That was the safer path.

           Or…

           Or she could take a risk and follow the path they were currently on, where soft touches may or may not lead to more intimate activities.  She only had to be brave enough to find out.

           Killian’s hand moved past her knee and onto her thigh.

           On a whim, Emma reached into her pocket and pulled out a d20.  She grabbed Killian’s hand and place the die in the middle.

           “Roll a seduction check,” she whispered.

           Killian blinked.

           “Do…” he started, but paused to swallow to before continuing.  “Do I use my charisma modifier for that?”

           Emma nodded.

           Killian shook the die in his hand and tossed it on the table.  He turned his head to watch until it came to a stop just before it could topple off the edge.

           “I can’t see what it is,” he murmured.

           Emma reached up and turned his face back toward hers.

           “It doesn’t matter,” she said a moment before she leaned forward and kissed him.

 

 


	2. Chapter 2

**Notes for the Chapter:**

> Once again, this has been Beta read by the amazing Mishasbabyminion, you should check her out on Tumblr (mishasbabyminion.tumblr.com/)

           

_Emma reached up and turned his face back toward hers._

_“It doesn’t matter,” she said a moment before she leaned forward and kissed him._

* * *

 

           Killian let out a small groan before eagerly returning her kiss.  His stubble rubbed against her cheeks, which was an unfamiliar but not unpleasant feeling.  She ran her hand along his neck and into his hair.  This elicited another low groan, which sent a shiver down Emma’s spine.

           Spurred on by his reaction, Emma scooted forward until her ass was resting against his leg.  Closer now, she trailed her other hand up Killian’s front until she was able to caress the chest hair constantly left exposed by his habit of leaving the top few buttons of his shirts undone.

           The hand that had been resting on her hip crept upward and Killian’s fingers dipped below the hemline of her top to rest on the small of her back.  His other hand made its way into her hair and with a little tug, tilted Emma’s head upward.

           Killian’s lips left hers so mark a trail of kisses down her throat.  He kissed along one collarbone, then the other, before burying his face in the curve of her neck.  He nipped the soft skin lightly with his teeth before soothing it with his tongue.

           Emma moaned.

           The hand on her back pressed against her, urging her farther forward until she was fully seated on his lap.  She could feel his hardness against her leg and she started to rock against it as Killian moved his attentions back up her neck.  Her nails dug into Killian’s chest when he found the sensitive spot behind her ear.

           He chuckled and tested the same spot behind her other ear, which elicited a similar response.  “You make the loveliest noises,” he whispered in her ear.

           Emma pulled Killian’s head back and pressed her lips against his again.  The kiss quickly became a battle between tongues, lips, and teeth.  At the same time, she quickly undid the buttons of Killian’s shirt so she could explore his chest.  He had plenty of chest hair, as she suspected, but it was softer than she would have thought.  She dragged her nails down his chest, enjoying the way the muscles jumped in response, until they came to rest at the waistline of his jeans.  She toyed with the buckle of his belt.

           Killian pulled back.

           “Are you sure about this Emma?”

           Emma leaned forward and licked along the ridge of Killian’s ear before whispering “yes”.

           Killian urged Emma to stand up, which she did, and he followed suit.  He slid his hands under the hem of her shirt, tickling the skin as he pulled it over her head.  She’d worn her favorite ‘comfy’ bra that day, but Killian didn’t seem to care as he had it undone and decorating the floor a moment after.  He caressed both her breasts in his hands and teased the nipples with his thumbs until they hardened.

           Emma’s eyes closed and her head tilted back at the wonderful feeling.  She gasped when Killian licked one nipple, then the other, before taking the first into his mouth.  He teased it with his tongue and bit just hard enough to stay within the bounds of pleasure.

           While his attention was on her breasts, Emma worked at undoing Killian’s belt.  She let out a growl when it proved more difficult than anticipated.  Killian’s laugh reverberated around the nipple he was teasing and Emma’s growl shifted into a moan.  He lifted his head, her nipple releasing with a pop.

           “Having trouble?” He said with a mischievous smile.

           Emma gave his belt a yank in answer, which elicited another laugh.  But he dropped his hands down to his waist and undid the offending buckle.  Emma roughly undid the button and zipper of his jeans before she reached her hand inside to grasp his stiff length.

           With one hand, Emma ran her fingers along Killian’s cock as far as she could and with the other, she started pushing his jeans down his hips.  Once they were out of the way, she was able to pull him free from his boxers.  Killian let out a strangled sounding moan when she stroked her hand along his thick, hard cock.

           Oh.  Oh yes.

           Emma wanted to continue her fondling, but Killian nudged her hand away before he bent down to fully remove his jeans.  She whistled when he stood back up, naked but for a necklace and a few tattoos.

           Killian raised his brow and nodded at her own pants.  Emma undid the button and quickly shoved both pants and underwear off in one movement.  She nearly toppled over when stepping out of them, but Killian grasped her hips from behind to steady her.  Feeling his cock against her, Emma pushed her ass backward to rub against it.  His grip tightened.

            When she stood up, his arms wrapped around her waist and pulled her back against his chest.  Killian’s lips kissed their way up her neck. He teased the same spot behind her ear he had discovered earlier while he softly rocked against her.  Emma opened her legs just enough for him to slip between her folds with a dip of his hips.

           “Condom?” He whispered in her ear.

           Emma drop her head back onto his shoulder.

           “Downstairs? Maybe?”

           Light pressure on her hips guided Emma toward the rooftop door.  As amazing as it would have been to have sex on the rooftop patio in the warm night air, it was probably better they go inside.  They didn’t need to give Jefferson’s neighbors a show.

            Emma pulled Killian down the stairs and into the guest room she had claimed earlier in the night.  She pulled open the drawer of the bedside table, hoping Jefferson may have left a box there at some point.

           The only thing inside was a hairbrush, for some reason.

           She growled.

           A cheerful “Ah-ha” came from behind Emma

           “Fear not, fair maiden, I have found the treasure!”  Killian stepped from the bathroom with a foil wrapped package held over his head.

           Emma couldn’t help but laugh.  A six-foot something, semi-hairy, totally nude man stood before her with a condom in one hand and a grin like that of a child who found his Christmas presents early.  Killian waggled his brows as he came to join her by the bed.     

           He pressed his lips against hers.  “Now where were we?” He asked between kisses.

           Emma wrapped her hand around his cock and gave it a soft tug.

           Killian slipped his hand between her legs until he reached her clit.  Her hips gave an involuntary jump when he teased his finger across it a couple times before continuing his exploration.  When he found her entrance, he slowly slipped his finger inside and Emma rocked her hips forward.  After a few moments, he slipped a second finger inside.

           It took a lot of effort for Emma to concentrate on the cock she had in her hand while Killian fingered her.  She ran her fingers through the curly hair at its base before she slip her hand back up its length.  As she circled the head with her thumb, she could feel a bit of wetness being spread about.

           Killian’s thumb pressed against her clit and Emma’s concentration broke.  Her head dropped forward and both her hands came up to grasp Killian’s shoulders as she rode the rising wave of pleasure.  Killian increased the pace of his fingers and continued to tease Emma’s clit until she peaked.

           Emma pressed her face against Killian’s chest to muffle the moans of her orgasm.  Killian hummed and whispered endearments in her ear as she rode it out.  When her muscles went slack, he gently removed his fingers from within her and guided her down onto the bed.

           Foil ripped and through hooded eyes, Emma watched as Killian rolled the condom over his cock.  He smiled as he moved to join her on the bed.

           “Having you fall apart on my hand was beautiful, you know” he murmured as he covered her body with his.  “But next time, I want to see your face when you cum.”

           Emma felt herself blush at his words, but hoped Killian would attribute the extra color in her face to her orgasm minutes earlier.  The kiss he placed on her cheek as he positioned himself just outside her vagina said otherwise.  Emma lifted her left leg and rested it against his hip to give him more room.

           Killian pressed forward, slowly.  She’d known from her exploration earlier that he was on the thicker side, but she was still unprepared for how much he stretched her as he entered.  Emma took a deep breath and let it out slowly.   

           “Are you alright?” Killian’s eyes were bright blue as he inquired about her comfort.

           Touched, Emma rested her hand on his cheek as she nodded.  To show him just how alright she was, she lifted her hips to press him even deeper inside.  His eyes fluttered and he groaned.

           He started slow, pulling no more than an inch out before pressing back in.  Emma rocked her hips with his movement.  He picked up the pace before long and the sound of skin slapping skin could be heard.             

           Emma adjusted her leg to wrap it around Killian’s hip and pressed her heel into the firm muscles of his ass.  She braced her other foot on the bed and met him thrust for thrust.  Just as she could feel herself nearing another orgasm, Killian slowed to a stop.

            The noise of frustration Emma made was somewhere between a whimper and growl.

           Killian chucked.  He pulled the leg that was wrapped around his hip free and stretched it skyward.  He kissed the soft skin behind Emma’s knee before he placed the leg on his shoulder.  Emma wasn’t sure she was flexible enough for this position, but when he thrust forward and hit her g-spot, she was damn well going to hold it as long as she could.  One of Killian’s hands squeezed between them and softly circled her clit

           Emma’s second orgasm built quickly and it broke before she knew it.  Her head thrashed back and forth and her hands buried themselves in the bedspread as waves of pleasure rolled through her.

           “Absolutely gorgeous,” she heard from above her.  When she opened her eyes once her orgasm had subsided, Killian was staring down at her with a sly smirk.  After she moved her tired leg, Emma reached up and grabbed him by his hair and pulled his face down to hers.  They battled for dominance of the kiss, lips, teeth, and tongues clashing.

           In an attempt to get the upper hand, Emma slid her hands down Killian’s chest.  When she reached his nipples, she gave each a tight squeeze.  Killian’s head lifted with a pleasurable hiss.  With him momentarily distracted, Emma maneuvered her right leg until it pressed it against Killian’s hip.  With a heave, she toppled him off of her and onto the bed and quickly climbed on top of him.

           Emma lifted herself up so she could position Killian’s cock at her entrance and slowly sank back down upon it.  

           “Oh yes…” Killian whispered.  He rested his hands on her hips, but made no attempt to guide her movement.  At first all she did was rock, adjusting to the new position.  But soon she began to use her legs to lift herself up and Killian thrust upward to meet her as she came back down.  She was almost dislodged when he had to adjust his legs for better leverage, but he kept her steady.

           He was quite a sight, Killian was, laid out beneath her.  His hair was a mess, his pupils were dilated, and there were red, crescent shaped marks along his shoulders from where her nails had dug into his skin.  The chest hair she had enjoyed earlier was on full display.  It was thickest on his pecs before it formed a trail down his stomach, which she now knew ended at the bush of hair around his cock.  She had never had a specific affinity for hairy men before, but she found that she quite liked what Killian had.

           Sweat dripped down Emma’s spine as the muscles in her thighs began to burn.  While she loved being on top during sex, she also knew she wouldn’t be able to maintain it for long.  Seeking one last climax, Emma purposefully fell forward and braced one hand next to Killian’s head, using the other to rub her clit.

           The pace of Killian’s thrusts increased and he began to guide the movement of her hips.  He tried a few different angles before he found one he seemed to like.  Which was fine by Emma, since it was also a great angle for her and she quickly crested her third climax of the night.

           Emma threw her head back as she came and bit her lip to keep from screaming too loudly as the orgasm washed over her.  It lasted longer than the others; Killian’s steady thrusts drawing it out.  As it ended, her muscles started to give out.  Her forehead hit Killian’s with a solid thunk.

           Just as she was about to apologize, Killian let out a loud groan and his hips jerked.  She could feel his cock twitching inside her as he came.  A string of obscenities with her name mixed in tumbled from his lips.

           His eyes had closed as he came, but when they opened again they stared straight into Emma’s own.  Normally, she would have shied away from such an intimate post-coital moment, but she couldn’t bring herself to look away.  There was no judgement in his eyes; no hesitation as he lifted his head just enough to place a soft kiss on her lips.

           “That was amazing,” he whispered as he wrapped his arms around her waist and pulled her fully down on top of him.  Emma relaxed into his embrace, though she did move her head so they could both breathe a bit easier.  She rested it on his shoulder and idly ran her fingers through his chest hair.

           They stayed that way for a few minutes, just enjoying the afterglow, until Killian’s cock began to slip from within Emma.  To avoid a mess, Killian carefully removed himself from the bed to deal with the condom.

           Usually, it was at this point that Emma would begin to collect her things and leave.  Or on the rare occasion that she brought someone back to her place, begin dropping hints that it was time for him to go.

           But as she watched Killian through the open bathroom door, all she could do was smile.  She felt… almost giddy.  The urge to leave, to run, to distance herself from a sexual partner was there, but it was overshadowed by how good she felt.  This had been much more than sex to satisfy biological urges.  There was something else there and Emma knew she would never get a chance to find it if she left now.

            So she stayed.

           And so did he.

**Notes for the Chapter:**

> I do hope you have enjoyed my cocky submission for CSCocktoberfest 2018! I do plan at least one more fic with these two nerds, so keep an eye out for it!


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